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Research Article z Available online at http://www.journalcra.com INTERNATIONAL JOURNAL OF CURRENT RESEARCH International Journal of Current Research Vol. 10, Issue, 08, pp.72879-72883, August, 2018 ISSN: 0975-833X RESEARCH ARTICLE NEW ISOFLAVONOID FROM THE ROOTS OF ALLEXIS OBANENSIS (VIOLACEAE) AND EVALUATION OF ANTIBACTERIAL, ANTIOXIDANT AND ANTIPLASMODIAL ACTIVITIES 1,*Nganso Ditchou Yves Oscar, 2Ndogo Eteme Olivier, 2Zondegoumba Ernestine, 3Mala Opono M. T. G. and 2Nyasse Barthelemy 1Department of Chemistry, Faculty of Science, University of Maroua, Cameroon 2Department of Organic Chemistry, Faculty of Science, University of Yaounde I, Cameroon 3Department of Biochemistry, Faculty of Science, University of Yaounde I, Cameroon ARTICLE INFO ABSTRACT Article History: In the search for new compounds endowed with antibacterial, antioxidant and antiplasmodial Received 22nd May, 2018 properties in Cameroonian pharmacopoeia, a new compound was established using spectroscopic Received in revised form analysis techniques. The compound was isolated from the ethyl acetate fraction of Allexis obanensis. 14th June, 2018 The antibacterial, antioxidant and antiplasmodial activities of this compound isolated were assessed in Accepted 27th July, 2018 st this study. It showed good antibacterial activities, good antiplasmodial activity against the Published online 31 August, 2018 chloroquine-sensitive Plasmodium falciparum 3D7 strain but has presented a weak antioxidant activity. Key Words: Antibacterial, Antioxidant, Antiplasmodial, Isoflavonoid, NMR Structure elucidation, Natural products. Copyright © 2018, Nganso Ditchou Yves Oscar et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Citation: Nganso Ditchou Yves Oscar, Ndogo Eteme Olivier, Zondegoumba Ernestine, Mala Opono M. T. G. and Nyasse Barthelemy. 2018. “New isoflavonoid from the roots of allexis obanensis (violaceae) and evaluation of antibacterial, antioxidant and antiplasmodial activities”, International Journal of Current Research, 10, (08), 72879-72883. INTRODUCTION 7-hydroxy-3-(3-hydroxy-4- methoxyphenyl) -5-methoxy-4H- chromen-4-one (1) which was extracted from the roots of Allexis obanensis belonging to the family Violaceae, is Allexis obanensis. We also evaluated the antibacterial, commonly distributed from Congo to Cameroon (Hutchinson, antiplasmodial and antioxidant activities of this compound. 1954). Violaceae plants have been constantly used in traditional medicine to treat many diseases caused by RESULTS AND DISCUSSION pathogenic agents. The bark of Allexis cauliflora are used to treat fever and syphilis (Achoundong, 2010; Achoundong, The ethyl acetate fraction of Allexis obanensis roots was 1998). Allexis genera have been reported as matrix purified by column chromatography on silica gel from which metalloproteinase inhibitors (Nganso et al., 2011), antioxidants we obtained one new isoflavonoid. The new isoflavonoid was (Vukics et al., 2008), stomach aches and antiplasmodials obtained in the form of a white powder in the CH2Cl2/MeOH (Moon, 2007), but experiments to isolate antiplasmodial and (50:1) solvent system. It showed the base peak of the molecular antioxidant agents from Allexis obanensis were not conducted. ion at m/z = 314.1236 (M + Na)+, (calcd. 312.10) in HRESI Despite the availability of this ethno pharmacological MS, corresponding to the formula C17H14O6Na. the UV information, there is no phytochemical report published on spectrum showed absorption bands at ƛmax 241, 248 and Allexis obanensis to date. In the present study, we report the 277nm, suggesting an isoflavonoid ring (18). The IR spectrum isolation and structural elucidation of a new compound named presented vibration bands at vmax 3324 (hydroxyl groups) 1630 and 1580 cm-1 (aromatic chain).On its 1H NMR spectrum, we observed a doublet of doublet of 1H integration at δ = 7.15 *Corresponding author: Nganso Ditchou Yves Oscar ppm (J = 8.2, 1.9 Hz) and an integration doublet 1H at δ = 6.93 Department of Chemistry, Faculty of Science, University of Maroua, Cameroon ppm (J = 1.9 Hz) attributable to H-6'and H-2' respectively. DOI: https://doi.org/10.24941/ijcr.32154.08.2018 72880 Nganso Ditchou Yves Oscar et al. New isoflavonoid from the roots of allexis obanensis (violaceae) and evaluation of antibacterial, antioxidant and antiplasmodial activities An integration doublet 1H at δ = 6.84ppm (J = 8.2 Hz) the new isoflavonoid shows that the CMB/CMI ratio is 2 for attributable to H-5'. CM64, BM67, ATCC8739, EA289, PS299645,ATCC11296, and EA294 strains. Antioxidant activities were achieved by two These three signals indicate a disubstitution of ring B. Two complementary tests, namely the DPPH assay for radical- doublets of integration 1H each, the first at δ = 6.28 ppm (J = 2 scavenging activity and the Ferric reducing-antioxidant power Hz) and the second at δ = 6.42 ppm (J = 2 Hz) attributable to (FRAP) assay for assessing reducing power. The scavenging H-8 and H-6 respectively indicating a disubstitution of ring A activity of DPPH is considered as classic, simple, rapid and in positions 5 and 7. Two singlets of integration of 3H at δ = inexpensive method for evaluating antioxidant properties. This 3.91 and 3.9 ppm revealing the presence of two methoxyl method is based on the ability of compounds to act as H donors groups in the molecule. The analysis of the spectrum relative to to reduce free radicals. However, this method is unable to the HSQC experiment makes it possible to assign the signals of highlight the reducing power of an antioxidant compound. For the protons to the corresponding carbon atoms thus: The H- this reason, the FRAP assay was added as a complementary 6'allows the attribution of the signal at δ = 115.4 ppm to the method (Messi et al., 2016). carbon atom C-6'. H-2'allows the assignment of the signal at δ = 120.8 ppm to the carbon atom C-2'. H-5'allows the This table shows that compound 1(07.50±0.48) has presents a assignment of the signal at δ = 112.4 ppm to the C-5' carbon weakly DPPH radical scavenging activity than the standard atom. The two families of protons of the methoxyl groups reference ascorbic acid (SC50 = 4.50 mM). The reducing power carried the carbons at δ = 55.6 ppm; δ = 48.01 ppm. According assay is based on the reduction of Fe3+ in potassium to the information collected from the HMBC spectrum, the H- ferricyanide to Fe2+ which forms a blue complex. The 2'and H-6' protons show: Two correlation spots with the same formation of this blue complex is monitored at ƛ= 593 nm. The carbon atom at δ = 146.65 ppm which can only be attributed to greater the reducing power of the analyte, the greater the carbon C-4. This same carbon atom shows a correlation spot concentration of the complex formed, leading to higher with methoxyl at δH = 3.84 ppm (δ C = 55.6 ppm), this absorbance values. The high antioxidant activity of phenolic supposes that this methoxyl group is carried by the C-4'carbon. substances is often attributed to their -OH moieties (18). These Two correlation spots with a carbon atom at δ = 148.8 ppm are potent H donors because they allow the delocalization of attributable to C-2. The H-5'proton shows two correlation electrons across the molecule. This fact can explain why this spots: The first with the carbon atom at δ = 125.0 ppm isoflavonoid has a weak antioxidant activity, because some - attributable to C-1' and the second with the carbon atom at δ = OH groups are methoxylated. We evaluated antiplasmodial 146.6 ppm attributable to C-3'. This attribution is confirmed by activity against the chloroquine-sensitive Plasmodium the correlation task of this ring (C-3') and H-2'. Oxygenated falciparum 3D7 strain for compound 1 and EA extract. In carbon C-7 at δ = 161.8 ppm shows three correlation spots: The conclusion, one new compound was isolated from the ethyl first with proton H-8 at δ = 6.28 ppm, the second with proton acetate root extract of Allexis obanensis. The antibacterial, H-6 at δ = 6.42 ppm and the third with protons of the methoxyl antioxidant and antiplasmodial activities of this compound group δ = 3.9 ppm, which predicts the position of the methoxy isolated were assessed in this study. Compound 1 (IC50 group on the C-5 carbon. This is confirmed by the correlation =12.47±1.44 µM) showed good antiplasmodial activity against between proton H-6 at δ = 7.9 ppm and oxygenated carbon C- the chloroquine-sensitive Plasmodium falciparum 3D7 strain 5. Hence the structure: but has presented a weak antioxidant activity.It also presented good activities against many bacterial strains. The Antimicrobial results: The results of antibacterial and antiplasmodial properties of compound 1 support the ethno- antifungal activities of EA extract and compound 1 from medicinal use of Allexis obanensis roots in the treatment of Allexisobanensis are presented in tables 1, 2, 3 and 4.The malaria and stomach aches. activity of ethyl acetate was not very different from that of compound 1. Nine strains of Gram-negative bacteria including Experimental reference strains (ATCC) and multi-resistant clinical isolates were used. These strains belonging to different bacterial General experimental procedures: Melting points were species are distributed as follows: determined on an Electro thermal I A 9000 series digital A strain of Escherichia coli (ATCC8739). melting point apparatus and were uncorrected. The UV spectra A strain and three clinical isolates of Enterobacter were recorded on UV-570/VIS/NIP and Shimadzu UV- aerogenes (ATCC13048; CM64; EA289; EA294). 24012A double-beam spectrophotometers. IR measurements were obtained on a PerkinElmer (model 1600) FTIR Two clinical isolates of Enterobacter cloacae 1 13 (BM67,K2). spectrometer. The 1D ( H, C, DEPT) and 2D (COSY, NOESY, HSQC and HMBC) NMR spectra were recorded in A clinical isolate from Providencia stuartii DMSO-d6 and MeOH-d4 using a Bruker 600 (600 MHz for (PS299645).
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